JP5683877B2 - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
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- JP5683877B2 JP5683877B2 JP2010193140A JP2010193140A JP5683877B2 JP 5683877 B2 JP5683877 B2 JP 5683877B2 JP 2010193140 A JP2010193140 A JP 2010193140A JP 2010193140 A JP2010193140 A JP 2010193140A JP 5683877 B2 JP5683877 B2 JP 5683877B2
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- light emitting
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- organic light
- electrode
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- 239000010410 layer Substances 0.000 claims description 212
- 238000002347 injection Methods 0.000 claims description 66
- 239000007924 injection Substances 0.000 claims description 66
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 38
- -1 anthracene compound Chemical class 0.000 claims description 33
- 239000010408 film Substances 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 27
- 230000005525 hole transport Effects 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003277 amino group Chemical class 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 13
- 125000004431 deuterium atom Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001725 pyrenyl group Chemical group 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
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- 230000008569 process Effects 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004896 high resolution mass spectrometry Methods 0.000 description 11
- 238000004528 spin coating Methods 0.000 description 11
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- 238000001771 vacuum deposition Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 229940126214 compound 3 Drugs 0.000 description 9
- 238000000151 deposition Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
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- 239000011777 magnesium Substances 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 4
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 4
- 229940126639 Compound 33 Drugs 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- RJLKIAGOYBARJG-UHFFFAOYSA-N 1,3-dimethylpiperidin-2-one Chemical compound CC1CCCN(C)C1=O RJLKIAGOYBARJG-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- CZYAFTZIQWCKOI-UHFFFAOYSA-N 1,5-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1Br CZYAFTZIQWCKOI-UHFFFAOYSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical class C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- CRGSMSNUTNRNQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=CO1 CRGSMSNUTNRNQM-UHFFFAOYSA-N 0.000 description 1
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
- DJBISLQGYCNPQJ-UHFFFAOYSA-N CCCC1(CC1)c(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2ccccc2)[n]1-c1ccccc1 Chemical compound CCCC1(CC1)c(cc1)ccc1-c1nnc(-c(cc2)ccc2-c2ccccc2)[n]1-c1ccccc1 DJBISLQGYCNPQJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 1
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Description
<合成例1:化合物3の合成>
1,5−ジブロモナフタレンを8.57g(30mmol)、ベンゾフェノンヒドラゾンを7.1g(36mmol)、t−BuONaを4.3g(45mmol)、Pd(OAc)2を0.13g(0.6mmol)そして2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルビフェニルを0.29g(0.6mmol)を、トルエン80mLに溶かした後、90℃で3時間撹拌した。常温に冷やした反応物に蒸溜水を加え、ジエチルエーテル100mLで二回、ジクロロメタン100mLで一回抽出した。集められた有機膜を硫酸マグネシウムで乾燥して濾過した後、溶媒を蒸発させて得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体1を13.9g(収率90%)得た。生成された化合物は、HR−MS(高分解能質量分析)を使用して確認した。
C36H28N4計算値:516.2314;実測値:516.2315
中間体1を10.3g(20mmol)、p−トルエンスルホン酸一水和物を7.6g(40mmol)そしてメチルエチルケトンを10mLの混合物に、トルエン50mLを加えた後、110℃で24時間撹拌した。常温に冷やした反応物に蒸溜水を加え、ジエチルエーテル100mLで二回、ジクロロメタン100mLで二回抽出した。集められた有機膜を硫酸マグネシウムで乾燥して濾過した後、溶媒を蒸発させて得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体2を3.78g(収率72%)得た。生成された化合物は、HR−MSを使用して確認した。
C18H18N2計算値:262.1470;実測値:262.1472
中間体2を2.62g(10mmol)、9,9’−ジメチル−2−ブロモフルオレンを3.29g(12mmol)、t−BuONaを2.9g(30mmol)、Pd2(dba)3を366mg(0.4mmol)そしてP(t−Bu)3を80mg(0.4mmol)を、トルエン60mLに溶かした後、90℃で3時間撹拌した。この反応が完結した後、常温に冷やし、これを蒸溜水とジエチルエーテル50mLとで三回抽出した。集められた有機膜を硫酸マグネシウムで乾燥させて溶媒を蒸発させ、得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、化合物3を4.53g(収率70%)得た。生成された化合物は、HR−MSとNMR(核磁気共鳴分析)とを使用して確認した。
C48H42N2計算値:646.3348;実測値:646.3352
1H NMR(CDCl3、400MHz)δ(ppm)7.82(m、4H)、7.76(d、2H)、7.57(d、2H)、7.53(d、2H)、7.23(t、2H)、6.96(t、2H)、6.36(d、2H)、6.00(dd、2H)、2.94(s、6H)、2.22(s、6H)、1.85(s、12H)
中間体1を10.3g(20mmol)、p−トルエンスルホン酸一水和物を7.6g(40mmol)そしてベンジルフェニルケトンを15.70g(80mmol)の混合物に、エタノール80mLとトルエン80mLとを加えた後、110℃で24時間撹拌した。常温に冷やした反応物に蒸溜水を加え、ジエチルエーテル100mLで二回、ジクロロメタン100mLで二回抽出した。集められた有機膜を硫酸マグネシウムで乾燥させて濾過した後、溶媒を蒸発させて得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体3を3.11g(収率61%)得た。生成された化合物は、HR−MSを使用して確認した。
C38H26N2計算値:510.2096;実測値510.2099
上記した化合物3の合成方法において、9,9’−ジメチル−2−ブロモフルオレンの代わりにブロモベンゼンを使用した他は同様の方法で、化合物12を75%の収率で合成した。生成された化合物は、HR−MSとNMRとを使用して確認した。
C50H34N2計算値:662.2722;実測値:662.2723
1H NMR(CDCl3、400MHz)δ(ppm)8.37(d、2H)、7.99(d、2H)、7.57−7.25(m、26H)、7.05(dd、4H)
カルバゾールを3.34g、(20mmol)、1,4−ジブロモベンゼンを12g(50mmol)、CuIを760mg(4mmol)、K2CO3を11g(80mmol)そして18−Crown−6を100mg(0.4mmol)を、1,3−ジメチル−3,4,5,6−テトラヒドロ−(1H)−ピリジノン(DMPU)50mLに溶かした後、170℃で8時間加熱した。常温に冷やした後、固体物質を濾過し、濾液にアンモニア水少量を添加した後、ジエチルエーテル100mLで三回洗浄した。洗浄されたジエチルエーテル層を硫酸マグネシウムで乾燥させた後、減圧乾燥して粗生成物を得て、シリカゲル・カラムクロマトグラフィで分離精製し、中間体4を固体で4.83g(収率75%)を得た。生成された化合物は、HR−MSを使用して確認した。
C18H12BrN計算値:321.0153;実測値:321.0151
上記した化合物3の合成方法において、9,9’−ジメチル−2−ブロモフルオレンの代わりに中間体4を使用した他は同様の方法で、化合物32を72%の収率で合成した。、生成された化合物は、HR−MSとNMRとを使用して確認した。
C54H40N4計算値:744.3253;実測値:744.3253
1H NMR(CDCl3、400MHz)δ(ppm)8.11(d、4H)、7.82(d、2H)、7.77(s、2H)、7.71(d、4H)、7.37−7.20(m、16H)、2.29(s、6H)、2.22(s、6H)
ブロモアセトフェノン3.98g(20mmol)をジメトキシエタン100mLに溶かし、2−アミノピリジン2.0g(20mmol)を入れた。常温で5時間撹拌した後、120℃で12時間撹拌した。この反応が完結した後、常温に冷やし、溶媒を除去した後でジクロロメタン100mLを入れた。10%重炭酸ナトリウム水溶液を入れ、pH10に合わせた後、ジクロロメタン100mLを利用して抽出した。集められた有機膜を硫酸マグネシウムで乾燥させて溶媒を蒸発させ、得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体5を2.4g(収率65%)得た。生成された化合物は、HR−MSを使用して確認した。
C13H10N2計算値:194.0844;実測値:194.0845
中間体5を2.52g(13mmol)を、ピリジン50mLに溶かし、ヨード4.95g(19.5mmol)を入れた。50℃で5時間撹拌した後、シュウ酸水溶液を入れて反応を終結した。ジクロロメタン50mLを利用して抽出した後、集められた有機膜を硫酸マグネシウムで乾燥させて溶媒を蒸発させ、得られた残留物を、シリカゲル・カラムクロマトグラフィで分離精製し、中間体6を3g(収率72%)得た。生成された化合物は、HR−MSを使用して確認した。
C13H9IN2計算値:319.9810;実測値:319.9814
上記した化合物3の合成方法において、9,9’−ジメチル−2−ブロモフルオレンの代わりに中間体6を使用した他は同様の方法で、化合物33を64%の収率で合成した。生成された化合物は、HR−MSとNMRとを使用して確認した。
C44H34N6計算値:646.2845;実測値:646.28457
1H NMR(CDCl3、400MHz)δ(ppm)8.88(d、2H)、7.88(d、2H)、7.85(s、2H)、7.80(d、2H)、7.48−7.26(m、10H)、7.25(d、2H)、6.90(t、2H)、2.33(s、6H)、2.29(s、6H)
アノードは、コーニング(Corning)15Ωcm2(1,200Å)ITOガラス基板を、50mm×50mm×0.7mmサイズに切り、イソプロピルアルコールと純水とを利用し、それぞれ5分間超音波洗浄した後、30分間紫外線を照射してオゾンに露出させて洗浄し、真空蒸着装置にこのガラス基板を配置した。
電子輸送層の形成時に、上記化合物3の代わりに化合物12を利用したことを除いては、実施例1と同様にして有機発光素子を製作した。
電子輸送層の形成時に、上記化合物3代わりに化合物32を利用したことを除いては、実施例1と同様にして有機発光素子を製作した。
電子輸送層の形成時に、上記化合物3代わりに化合物33を利用したことを除いては、実施例1と同様にして有機発光素子を製作した。
電子輸送層の形成時に、上記化合物3代わりに、既知の物質であるAlq3を利用したことを除いては、実施例1と同様にして有機発光素子を製作した。
Claims (16)
- 下記化学式1で表されるヘテロ環化合物:
前記R 1 またはR 6 はそれぞれ独立して、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基、フルオレニル基及びピレニル基から選択される非置換の1環ないし4環のアリール基またはカルバゾリル基;
非置換のC 4 −C 60 ヘテロアリール基;
非置換のC 5 −C 50 アリールアミン基;
重水素原子、C 1 −C 5 アルキル基、C 1 −C 5 アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン基で置換されたフェニル基、ナフチル基、ビフェニル基、ターフェニル基、アントラセニル基、フルオレニル基及びピレニル基から選択される1環ないし4環のアリール基またはカルバゾリル基;
重水素原子、C 1 −C 5 アルキル基、C 1 −C 5 アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基、ハロゲン基またはC 5 −C 10 ヘテロアリール基で置換されたC 4 −C 60 ヘテロアリール基;
または重水素原子、C 1 −C 5 アルキル基、C 1 −C 5 アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン基で置換されたC 5 −C 50 アリールアミン基である。 - 前記R1及びR6が同一であるか、R2及びR7が同一であるか、R3及びR8が同一であるか、R4及びR9が同一であるか、またはR5及びR10が同一である、請求項1に記載のヘテロ環化合物。
- 前記R2、R3、R7またはR8はそれぞれ独立して、メチル基またはフェニル基である、請求項1または2に記載のヘテロ環化合物。
- 第1電極と、
第2電極と、
前記第1電極と前記第2電極との間に介在された有機膜とを備える有機発光素子であって、
前記有機膜の少なくとも一つの層が、請求項1ないし4のうちいずれか1項に記載のヘテロ環化合物を含む、有機発光素子。 - 前記有機膜が、電子注入層または電子輸送層を含む、請求項5に記載の有機発光素子。
- 前記有機膜が、電子注入機能及び電子輸送機能を共に有する単一膜を含む、請求項5に記載の有機発光素子。
- 前記有機膜が、発光層を含む、請求項5に記載の有機発光素子。
- 前記有機膜が発光層を含み、前記ヘテロ環化合物が、蛍光またはリン光のホストとして使われる、請求項5に記載の有機発光素子。
- 前記有機膜が発光層を含み、前記ヘテロ環化合物が、蛍光ドーパントとして使われる、請求項5に記載の有機発光素子。
- 前記有機膜が、発光層、電子注入層または電子輸送層を含み、前記発光層は、アントラセン化合物、アリールアミン化合物、またはスチリル化合物を含む、請求項5に記載の有機発光素子。
- 前記有機膜が、発光層、電子注入層または電子輸送層を含み、前記発光層が、リン光化合物を含む赤色発光層、緑色発光層、青色発光層または白色発光層を含む、請求項5に記載の有機発光素子。
- 前記有機膜が、正孔注入層、正孔輸送層、電子阻止層、発光層、正孔阻止層、電子輸送層及び電子注入層からなる群から選択される1層以上の層を含む、請求項5に記載の有機発光素子。
- 第1電極/正孔注入層/発光層/第2電極の構造、第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/第2電極の構造、または第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極の構造を有する、請求項13に記載の有機発光素子。
- 1層以上の層が、前記ヘテロ環化合物を使用し、湿式工程で形成される、請求項5ないし14のうちいずれか1項に記載の有機発光素子。
- 請求項5ないし15のうちいずれか1項に記載の有機発光素子を備え、前記有機発光素子の第1電極が、薄膜トランジスタのソース電極またはドレイン電極と電気的に連結された、平板表示装置。
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